


Each Act is Virgin, Even the Repeated Ones

by Jessia



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Angel Mojo, Angst, Blow Jobs, Dream Sex, Established Relationship, First Time, Hurt/Comfort, John Winchester's A+ Parenting, Loss of Virginity, M/M, No Refractory Period, Past Abuse, Past Rape/Non-con, Praise Kink, Prostitution, Riding, Rimming, Teen Dean, Topping from the Bottom, Underage Prostitution, Underage Sex, Virgin Dean
Language: English
Status: Completed
Published: 2015-10-01
Updated: 2015-10-01
Packaged: 2018-04-24 07:10:24
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 7,743
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4910038
Author URL: https://archiveofourown.org/users/Jessia/pseuds/Jessia
Summary: <blockquote class="userstuff">
              <p>Sam walks in on Dean and Cas having sexytimes in the bunker and freaks out thinking Dean is under a spell. This leads to an awkward discussion of Dean's sexual past, and then Cas comforts his angsty hunter.</p>
            </blockquote>





	Each Act is Virgin, Even the Repeated Ones

**Author's Note:**

  * For [Teatimelady](https://archiveofourown.org/users/Teatimelady/gifts).



> Please see end notes for clarification of tags if you are uncertain about any of them. Things get graphic, so please only proceed if that's something you are comfortable reading.
> 
> Also note that past tense = the present, and present tense = the past. Because I'm evil.
> 
> Title is a quote by Rene Char.
> 
> Thanks go out to my best friend and awesome beta, Teatimelady.

Sam couldn’t believe he’d gotten all the way into town on his grocery run before realizing he’d left his wallet back at the bunker. He was still rolling his eyes at himself as he pushed through the heavy front door, when a low sound made him stop short.

He listened intently for a few moments and heard it again – a pained moan. Hunter’s instincts on high alert, Sam pulled his gun and silently made his way down the stairs. Soon he could hear what sounded like a struggle coming from the library.

Rounding the corner, the younger Winchester couldn’t believe his eyes. Dean had their resident angel pinned to the library table, attacking him and ripping his clothes off as Cas struggled to fight him off.

Without another thought, Sam strode across the room and dragged his obviously cursed brother off the angel. Both Dean and Castiel stared at him in shock as he forcefully pinned his older brother to the wall.

“What the Hell, Sammy!?” Dean demanded. The blond’s shirt was torn from the earlier tussle, and his belt and fly were hanging open.

Sam ignored his outraged brother in favor of checking on his friend. “Cas, are you okay?” He glanced over his shoulder to find the angel sitting up and scooting off the table with a confused look on his face. He hiked his slipping slacks back up his slim hips and pulled the torn halves of his dress shirt together to cover himself as he moved towards the brothers.

Sam held out a hand to pause the angel’s forward movement. “Wait, Cas. Maybe you should stay back until we can figure out what curse or hex Dean has on him.”

“What the fuck are you talking about, Sam? I’m not cursed! Or hexed! Or anything else except about to kick my baby brother’s ass for cockblocking me!” Dean fumed.

“Exactly!” Sam declared. “What’s wrong with you that’s got you attacking Cas!?”

“Attacking?” Dean seemed at a loss for words.

The angel laid a palm on the younger Winchester’s shoulder, gently pulling him back to let Dean away from the wall. “Sam, Dean wasn’t attacking me. His actions were quite welcome,” Cas admitted sheepishly.

The tall man opened and closed his mouth to speak a few times before he shook his shaggy head to clear it. “Well, okay. But something’s still wrong! Dean, you’re totally straight! You’ve never had one bit of interest in guys!”

“Do you know how your brother lost his virginity, Sam?”

Sam looked from the now glowering angel to his brother with a look of ‘well, duh’ on his face. “Of course I do. You took Jenny Thomas to that make out spot in the Impala at the end of your sophomore year,” he stated with certainty. But that confidence began to fade as Dean refused to meet his eyes, and Castiel slowly shook his head.

“No, Sam,” Cas replied gravely.

Dean looked to the angel with pleading eyes. “Cas, don’t. _Please_.”

Castiel’s stern features softened slightly as he turned to the older Winchester. “I can tell him if you can’t,” he offered.

Dean seemed to deflate as he sat down heavily into a chair. “No, I’ll… I’ll do it,” he relented, but he refused to meet either his or Sam’s eyes.

“You remember the first time Dad went AWOL on us?”

Sam nodded even though Dean wasn’t looking at him. “Yeah, the summer I was eleven. He was supposed to be out hunting for a month, but he didn’t come back for three.”

“Yeah, that’s the one,” Dean confirmed. “We began running out of money around week six. I started skipping meals here and there and trying to find other ways to save so I could be sure we’d have enough to stay in the motel. Even that only helped so much-”

“You stopped eating,” Sam interrupted. “You came down with something, and always said you weren’t hungry. You lost a bunch of weight… You looked terrible. Wait, are you telling me you weren’t sick? Did you starve yourself, Dean!?” Sam demanded with genuine concern and a bit of anger.

Dean sighed and seemed to shrink into himself. “No, Sammy, not exactly. Not on purpose anyway…” The hunter rested his elbows on the table in front of him and leaned forward until his face was hidden in his hands before he continued. “I tried everything I could think of to earn extra cash, I really did. The local body shops didn’t believe a 15 year old had the skills to work on cars, no one would hire a kid too young to legally work, and I wasn’t even close to passing for 21 to get into bars and hustle pool. I had to do _something_ ,” at this Dean’s voiced cracked, and he had to pause and just breathe for a moment.

His brother’s uncharacteristic behavior was starting to worry Sam. “Dean?” he asked tentatively.

The older man let out a long breath before speaking again. “There was only one other thing I could think of. I knew if I hung around outside the right bars…” he trailed off for a moment. “I really didn’t think it would be a big deal. I mean, I’d been interested a few times before… A couple hours, a couple guys and I’d have enough for us to eat for the next few days.”

Cas, who’d stood silently behind Dean’s chair this whole time, watched as a dawning horror began to spread across the younger Winchester’s face.

“The first one wasn’t so bad. He was good looking enough, and I didn’t really mind going down on him,” Dean admitted.

_He’s only been outside the dive bar for about twenty minutes before he sees the blond surfer-type checking him out. Dean is in his tightest pair of dark wash jeans (the ones that make his ass look amazing) and a snug-fitting white tank top; he knows that showing off his wide shoulders and hunting-toned arms helps him look older than he is. His hair is tousled purposefully, and the black metal chain around his neck hits his collar bones just right._

_He’s nervous as hell, but leans one shoulder against the brick wall beside him to hide it as the older man approaches him. “Hey, there,” the man says in a friendly tone as he moves in close to Dean. He’s not yet up in his personal space, but he’s definitely closer than propriety would normally allow. “Aren’t you just the prettiest thing?”_

_A lazy smirk spreads across the teen’s face, and he cocks his hips out invitingly. “Aren’t I just?” he replies with a wink._

_This earns him a chuckle from the surfer-dude, and he relaxes marginally. It’s going pretty well so far, he thinks to himself. The guy is fairly handsome – shoulder-length tousled hair, warm brown eyes, angular jaw, and a kind smile that shows off perfect white teeth. His heartbeat picks up and his body heats in a pleasant way as the man leans in until their bodies are just barely brushing, and he runs the back of one finger gently down the side of Dean’s face letting his palm come to rest against the side of the teen’s neck._

_“Are you looking for some company?” Dean asks him, tongue darting out to lick his lips._

_He watches as the blond tracks the movement and those brown eyes dilate. “Mm hm,” he manages as his lips descend on Dean’s, his tongue easily swiping into the teen’s mouth through his parted lips. The kiss is passionate but languid, the older man exploring as his body presses Dean’s backward into the bricks. The blond is half-hard, but Dean’s teenage libido has him rock hard in mere moments. When the older man pulls back, Dean can’t help the choked-off noise that escapes his throat. “That mouth,” he trails off thoughtfully. “I wonder what it would take to get that mouth around my cock…?”_

_Dean grins, pupils blown and an excited flush across his cheeks. “Twenty and it’s all yours,” he purrs. Without breaking eye contact, the blond reaches into his back pocket and holds up a $20 bill between two fingers to show Dean before he slips it into the boy’s pocket, sliding his fingertips along Dean’s length as he pulls his hand out. Dean reins in a full body shudder, guiding the man around the corner into the alley and dropping gracefully to his knees._

_The man unbuckles his belt while Dean works down the zipper, and then he reaches in to pull him out of his boxers, and suddenly Dean has his first cock-that-belongs-to-someone-else in his hand. His eyes widen marginally and the nerves try to reappear, but then he glances upward through his long lashes and the lust combined with kindness he sees in the other man’s face is enough to settle him again._

_He begins with a tentative lick to the head, salty precome spreading across his tongue. It’s strange but not terrible, so he laps at it for a few moments before swirling his tongue around the crown. He hears encouraging noises, so he begins to experiment. He has absolutely zero practical experience with this – either giving or receiving – but a life lived hopping from one cheap motel to another means he’s seen plenty of porn from which to draw inspiration. He sucks hard on the head, earning a groan. Switches to kitten licks on the frenulum, resulting in soft sighs. When he takes the blond down as far as he can go without warning and begins bobbing enthusiastically, he elicits a gasp that echoes in the alleyway._

_The man above him leans forward over Dean just enough to brace himself with a hand on the brick wall. His other hand slides into Dean’s hair, just touching and guiding, not pulling. Dean’s pretty proud of the continued litany of sounds he’s wringing from the blond, and he continues his slide up and down the man’s cock, trailing his tongue along the underside with every drag out and sucking firmly with every thrust back in. When the older man’s breathing is down to harsh panting and continuous groans, Dean grabs his jeans-clad ass with both hands and lets just a hint of teeth into his actions, and it’s all over. The blond comes with a wail in a hot gush down Dean’s throat without warning, and the teen instinctively swallows in surprise._

_He pulls off gasping for air as the spent man grips the brick wall for long moments. He stands when the older man tucks himself back in and refastens his pants. “That was fantastic,” he whispers breathlessly before dragging Dean in by the back of the neck for a filthily thorough yet brief kiss and walking away without a look back._

“Got 20 bucks outta it, and I was feeling pretty cocky.” A mirthless grin flashed across what little was visible of his face for the briefest of seconds. “The next guy wasn’t nearly such a looker, but I figured ‘What the hell?’ easy money.” Dean huffed out a pitiful parody of a laugh. “Easy…”

_The bald middle-aged man would not have been Dean’s pick for a casual hookup by any stretch, but this is business, so Dean accepts his stuttering invitation into the alley. Sweaty hands slip and fumble on the fastenings of his belt and slacks, but he manages to free himself eventually as Dean lowers himself to the ground. The teen is surprised to find the slightly overweight man fully hard given how nervous he seems, but he doesn’t get much time to process the thought at all._

_Before Dean can lean in and get to work, the man grips his face hard, forcing his jaw open for him to shove inside all at once. The teen manages to gasp in just a bit of breath around his sudden mouthful, but exhales it forcefully only seconds later as the man’s whole body surges forward bashing the back of Dean’s head painfully against the brick wall. His vision swims momentarily from the knock, but he isn’t given any chance to gather himself before the man is thrusting in and out of his mouth quickly and viciously._

_He chokes every couple of thrusts as the cock is rammed into the back of his throat, and the tightening muscle causes the older man to groan obscenely and start a tirade of humiliating words. “Yeah, choke on it, you little slut. You just can’t get enough cock in that fucking mouth, can you?” Dean’s eyes begin to water with the combination of pain and lack of oxygen, but the pleading look in his face when his eyes find those of the other man just seems to encourage more abuse._

_The man continues to pound Dean’s face, pausing every now and then to hold the boy in place with his nose crushed into his pubic hair as his length ceases all of the teen’s ability to breathe. As the edges of Dean’s vision begin to dim, he starts to panic, trying vainly to pull back but stopped by the wall at his back and the large hand now closing around his throat. He’s full on crying now, sure that he’s about to die in some back alley and leave Sammy all on his own. But the choked sob Dean releases just before everything goes black seems to be just the thing to push the older man over the edge, bitter seed flooding his mouth and spattering his face as the man lets him go to collapse to the ground._

_Dean vaguely registers more insults and jabs as the man resettles his clothing and tosses some crumpled bills to the ground a few feet away. He notices the man laughing as he crawls to the money and pockets it, but he’s staying focused on not puking right now. Finally he hears the man walk away as he brings his hand down from the back of his skull to find his fingers coated in blood._

“He was - rough. He liked when I choked, and he held me down on him until I couldn’t breathe before he’d pull back. He called me names, and made fun of the tears streaming down my face. When he was done, he laughed at me gagging on his cum and threw the money down where I had to crawl for it. I don’t even think he gave me the full twenty; I never remembered to count it. I made it back to the motel room before I threw up. You were still asleep, just like I’d left you, so I took the hottest shower I could stand and brushed my teeth for half an hour before using half a bottle of mouthwash. I swore that I was never doing that again, but the next morning when I got back from the store and pulled out your favorite cereal… Your face just lit up, Sammy. I knew it would only be a day or two before we’d be out of money again, and we had no idea when, or if, Dad was coming back… So I went out the next night and the next night and the next night.”

Sam’s voice was barely more than a whisper, “You started looking tired all the time. And you said you didn’t want to eat because you felt nauseous.”

“My stomach couldn’t stand the thought of eating the food, knowing what I’d done to get it. It was enough for me that you weren’t going hungry, and I’d be able to pay the motel bill. But I had to stay out longer to make any decent amount of money. When we still hadn’t heard anything from Dad a couple of weeks later, I started to get really nervous about what we were going to do if he never came back. I’d gotten on speaking terms with some of the other,” Dean paused and gulped audibly before forcing out the next word, “ _whores_. They kept telling me I could earn more if I’d do more than blowjobs. I resisted up till that point, but if Dad wasn’t coming back I needed to suck it up and do what I had to.”

Sam had remained standing so far, but now collapsed into another chair, a barely-heard broken ‘no’ escaping his lips.

“It was awful,” Dean confessed.

_The scraggly ponytail and cut-off sleeves should be the first red flag, but Dean is determined to do this before he loses his nerve. The preliminaries are quick and minimal, Dean naming his price and the guy dragging him into the alley._

_Dean thought it would start with some kissing or at least a blowjob, but he is so wrong. Without a word, ponytail-guy shoves the teen face-first into the bricks and yanks his jeans and boxers to his knees. He kicks Dean’s feet as far apart as they’ll go, and his belt buckle clanks as he undoes his ripped jeans._

_Before he can process what’s going on, Dean feels a blunt pressure at his hole, and he begins to protest as he realizes that Mr. Ponytail isn’t planning on any prep. “Wait, no no no…” his words cut off in primal scream as the man’s large cock forces its way inside Dean’s dry, virgin hole._

_The breath is forced out of his lungs by both the weight of a heavy body slamming him into the wall and the agonizing stabs of pain that shoot up his spine with every thrust. It feels like he’s being torn apart from the inside, and he struggles to gasp air to form words. “Please!” he begs. “Stop,_ please! _”_

_The teen’s pleading draws a chuckle out of the larger man, and his hands grip bruises into the boy’s hips as his thrusts increase in both speed and force. Dean struggles harder when he realizes that the wetness he can now feel sliding down his thighs is his own blood, but the guy just pins him more securely with a forearm pressed across the back of his neck. The teen cries angry tears over being unable to stop some dumbass rapist trucker when he’s faced down and killed things that would probably scare the piss out of the guy._

_After what seems like forever, the guy grunts and spills himself inside Dean, and the teen takes the opportunity to elbow the man as hard as he can in the gut forcing him backward, his limp penis pulling out painfully with a sickening squelch of blood and come. He growls in pain before kicking the back of the boy’s knees causing him to collapse to the ground, and Dean is really thankful he insisted on his money up front._

_The man walks off cursing, leaving Dean struggling to stand and right his clothes with shaking hands._

“I turned the shower to scalding and scrubbed until my skin was raw. Then I just sat in the tub until the water ran cold.”

Sam could hardly speak now, but he forced his words out anyway. “I found you there. The water was freezing, and you were so out of it. You mumbled something about having a fever.”

“Yeah, you bundled me off to bed and played nursemaid until I felt better a few days later.” Dean couldn’t help the affection that crept into his voice at the memory of his baby brother devotedly caring for him. He quickly turned somber again. “It was the worst 20 minutes of my life, but I made what normally took three or four hours to earn. It got easier, if not more pleasant. I learned to prep myself before going out to minimize the pain and damage. I could usually get them to agree to a condom, but not always. I worried about catching something, but I couldn’t see where I had any other options. I made as much money as I could and stashed away what wasn’t used for the room or food. Finally Dad showed up, and I could stop going out. I kept the saved money on me at all times, so when Dad pulled another disappearing act the next summer, I was able support us off my savings. The times he vanished on us after that I was old enough to get honest work or to get into the bars to hustle pool.”

“Oh, God, Dean. I’m so sorry. I didn’t know how you kept us going when Dad split.” Sam looked stricken.

The older man finally looked up at the tone of his brother’s voice. “Sammy, no, it was _not_ your fault. I didn’t want you to know. I was very careful so you wouldn’t know,” he reassured.

Sam’s brain finally picked up on something Dean had said earlier. “Wait, you said you’d been interested in guys before that?”

“Yeah,” Dean confirmed.

“But not after? I mean, you’ve always been pretty vocal about being straight.”

Dean sighed. “I… looked,” he admitted. “But I never tried anything. I couldn’t ever bring myself to trust someone that way after everything.” A small smile crept onto the hunter’s face, and he ghosted his fingers over those of the angel that had found their way onto his shoulder at some point during his painful revelations. “Until I realized that I had the only person I could trust with my soul let alone my body right in front of my face.”

Sam smiled at that, and Dean thought he looked fairly close to tearing up like a girl as he said, “I’m really happy for you, Dean. And Cas. Sorry about the freak out.”

Dean submitted to his brother’s manly hugs for a moment before shoving him off playfully. “Yeah, yeah. Thanks, Samantha,” he groused with affection.

The younger Winchester rolled his eyes at the long-familiar insult. “Well, the whole reason I interrupted you guys was that I forgot my wallet on my grocery run. I’m gonna go grab it and head back into town.”

After swinging by his room to retrieve his wallet, Sam passed back by the library, pausing to throw over his shoulder, “But let’s agree to no more naked times in the public areas, huh?”

“I make no promises, Bitch!” Dean called to his brother’s retreating back.

“Jerk!” echoed back over the closing of the outer door.

Yeah, they were gonna be fine.

Dean turned to the angel behind him looking wrung out. Cas pulled Dean into his arms, and the blond wrapped his arms around his waist. “Are you alright?” Castiel inquired softly.

He pulled back but stayed in the circle of the shorter man’s arms and gave him a crooked smile. “Yeah, just tired.” He pressed a gentle kiss to the angel’s lips. “Think we could go take a nap?”

“Of course, Dean. Anything you want,” Cas agreed.

They retreated to Dean’s room and stripped down to boxers for Cas and boxer briefs for Dean before arranging themselves comfortably in the bed. Cas lay on his back with Dean tucked up to his side using his shoulder as a pillow. The angel enjoyed the simple press of skin to skin as his hunter’s breathing evened out.

Just when he thought the blond had dropped off to sleep, he heard an uncharacteristically timid-sounding, “Cas?”

“Yes, Dean?” he inquired softly.

“I wish you’d been the first,” he confessed in a rush.

Cas used one hand to gently tip Dean’s face up to his own. “I don’t.” At Dean’s confused and almost hurt expression, Castiel was quick to continue. “Though I would spare you the pain you went through, you would not be the man you are today without your past. And I am quite fond of the man you are today.”

That earned him a brief sleepy kiss before the hunter settled back down and drifted off.

_Castiel enters Dean’s dreamscape to find himself across the street from a run-down looking bar. He spots Dean amongst the few people milling about the entrance to the place, and the sight is almost surreal. He’s shorter than Cas now, only reaching as high as his nose. He’s muscled, but in the way of lanky youths instead of the compact strength the angel is accustomed to. His hair is so much blonder that when combined with the roundness of his face and the lack of creases at his eyes, the hunter looks unbelievably innocent._

_That air of innocence attracts attention from more than just Castiel, but the angel deflects the path of the miscreant with a ponytail away from Dean and approaches in his place. Those green eyes are just as mesmerizing looking up at him as they usually are looking down, but Cas is gratified to note that the young man seems just as caught up in his blue gaze._

_The angel reminds himself why he’s here, and steers things back on track. “How much for the night?” he quietly rumbles, and watches the teen’s eyes dilate slightly at the sound._

_“Uh…” is all Dean manages, as it seems he hasn’t thought this far ahead. Cas pulls out a roll of bills that has to be at least three or four grand, and the boy is momentarily stunned. “Wow. Yeah, you got someplace for us to go?”_

_It’s no time at all before they’re standing inside a room at the crummy yet clean little motel a couple blocks away, the décor on par with that of the motel room Sammy is sleeping in across town. An attack of nerves seems to hit Dean, and he combats it by practically launching himself at the brunet._

_Castiel allows unsteady hands to shuck the trench coat from his shoulders, but stills the shaking fingers that begin to fumble with his tie and shirt buttons. He cups the young man’s face with one large hand bringing their eyes to meet. “Hey,” he says gently, “There’s no rush…”_

_Dean seems to relax a bit at this. “Okay…?”_

_“Castiel,” the angel offers._

_“Okay, Cas,” he can’t help the twitch of a smile at the familiar nickname, “I’m Dean.”_

_“Hello, Dean.” The kiss he leans down and gives is sweet and almost chaste, and Dean just melts into it as their arms wrap around one another. The angel uses the hand at his cheek to tilt the teen’s head just so, and the kiss deepens. It’s a pleasant surprise when Dean is the one to lick at Cas’ mouth, begging for entrance, and he parts his lips willingly as he sinks his other hand into short blond locks._

_Dean’s arms are around the taller male’s waist, fingers clutching the white dress shirt, while they languorously explore one another’s mouths. Cas slides the hand from the teen’s face to his hip and pulls their bodies flush, erections pressing together, as he works his lips down over his throat. The surprised gasp that melts into a groan makes the angel smile against his skin. When he bites down gently on the spot between neck and shoulder, Dean’s whole body shudders, and he rucks the shirt from the waistband of Cas’ pants._

_The angel hums in satisfaction when Dean’s hands slip under the fabric and eagerly begin exploring the planes of his back. Castiel works his mouth back up to Dean’s lips, and this time he kisses with more heat – he can’t really help it, Dean in any form just_ **does** _things to him. This time when Dean starts on the buttons of the angel’s shirt, his hands are quick and steady, and soon the garment is forgotten in a puddle on the floor behind them along with his tie. The hands now sliding up his chest are familiar and foreign at the same time. Overall they’re the same size, but the fingers are thinner and missing the years of built up calluses that he’s used to._

_He strips Dean’s tee shirt over his head, and the frustrated whine he receives when their lips have to part makes him chuckle. Instead of diving back in as the teen clearly desires, Cas works his way back down the other side of his neck, nipping at a collarbone before continuing lower. The angel goes to his knees just as his lips close around one of the blond’s nipples, and Dean keens, gripping tight to broad shoulders. Castiel laves it for a few moments before switching to the other as his nimble fingers work open the fastenings of the young man’s jeans. He looks up to Dean’s face and is captivated for a moment by the way his teeth are sunken into his bottom lip. When their gazes meet, he quirks a questioning eyebrow while his fingertips slip beneath the waistband of his jeans and boxers, and Dean nods his head quickly._

_With permission granted, the angel slides the rest of the clothing down toned legs and coaxes Dean to step out of the tangle of them along with his boots and socks. The sight of Dean before him – flushed, hard, and dripping precum – makes his mouth water and breaths come faster. He leans forward to give a single lick across the head, and_ this _is familiar – the burst of flavor over his tongue that screams ‘Dean’ in his brain. Castiel is well practiced at this, so it’s nothing for him to slide his lips down and take Dean whole. The startled, “Fuck!” from above him is just as gratifying from young Dean as it is from older Dean._

_He hums before swallowing around the length in his throat, and he swears he hears Dean whine. He starts bobbing his head up and down Dean’s cock, licking and sucking as he goes. The angel pulls out all the stops; he knows every little trick that Dean loves – Dean himself taught him, after all – and he uses all of them._

_Cas loves how vocal this Dean is; he allows his moans and gasps to escape unabashedly in a way it took months to coax out of the older version. The younger man’s thighs begin to shake, and Castiel pulls his hands down to tangle in his dark hair, encouraging Dean to let go. His hands clench tightly as he pulls the angel on and off his dick, fucking his face. Cas groans appreciatively, and Dean is gone. “Oh, fuck! Cas!” The teen nearly screams as he comes hard down the older male’s throat, and his knees buckle. It’s only Cas catching him by the hips and guiding him to the bed that keeps him from collapsing to the floor._

_Dean looks on with half-lidded, pleasure-dazed eyes as Castiel licks stray drops of his come from his –_ **red, wet, used** _– lips while ridding himself of the last of his clothing. He’s still trying to catch his breath when those lips descend on his own, tongue swiping confidently into the warm cavern of his mouth, and he can taste himself there._

_When the kiss breaks, Cas reaches down to his discarded trench coat and pulls something from one of the pockets. Dean can’t help the nerves that leap to the surface once again as the angel climbs onto the bed next to him, bottle of lube in his hand. His anxiety must show on his face because after another swift kiss, Castiel is quick to reassure him, “This is for me, not you.”_

_Dean’s confused for a moment until the brunet arranges himself on his back with his head on the pillows and spreads his legs wide, weeping erection standing proud. Cas slicks the fingers of one hand before setting the bottle aside and lowering them between his thighs. He bypasses his cock completely because he’s not sure how long he’d last and circles his hole for a moment. He watches Dean’s transfixed face as he sinks the first finger into himself, and he smirks when he hears the boy’s breath catch._

_As he slowly works lube into his channel, he feels the bed shift when Dean leans up on an elbow to get a better view. It seems the blond isn’t aware he’s done so because he startles a bit when the angel speaks. “You can come over here for a better look if you like,” he rumbles. Cas has no choice but to chuckle when the teen moves so fast to comply that the sentence is barely all the way out before he’s settled on his knees between Castiel’s thighs._

_Cas’ second finger slips in along with the first, the slight stretch feeling so familiar, and he sighs a little in pleasure. Dean’s breathing, which had just begun to settle into a normal rhythm, picks up again as he watches the older male twist and scissor fingers into his own ass. He feels a flush of heat as he begins to harden once more. Dean opens his mouth as if to speak, stops, swallows hard, opens his mouth again… but words don’t come. Green eyes flick up from the erotic sight to catch blue watching him. “I-“ he pauses uncertainly, but Cas nods for him to go on. “Can… Can I help?” He asks, almost meekly._

_The unrestrained smile Cas grants him eases some of his tension. “Please, do.”_

_Dean uses the bottle of lube to slick up some fingers and leans forward with a hand beside the other man’s hip. He slowly works one digit in between the two Cas already has in himself, and the feeling is strange and thrilling. He didn’t know it would be this hot or this tight or that he would be able to feel Cas’ moan from the inside. They move together, working their entwined fingers in and out, and Dean feels as dazed as Castiel looks. When the brunet asks, “Please, Dean, more,” the teen adds another finger. He watches in awe as the angel’s hips roll, and his head is thrown back with a loud groan when he grazes over what must be his prostate._

_Dean likes the reaction so much that he rubs over the bundle of nerves again and again just to watch Cas begin to fall apart. When the older male is finally able to lock their gazes again, the heat and need Dean sees there is enough to make his mouth go dry. “Dean, do you want to fuck me?” his voice comes out like whiskey over gravel, making Dean’s stomach flip. The teen is so stunned by the offer that all he can do is nod._

_Castiel draws their fingers out of his body and places his clean hand on the boy’s chest. “Lie down,” he gently encourages. Theoretically, Dean knows the mechanics and logistics of sex, but right now in the moment his mind can only focus on the lust and need and want coursing through his body. The young man is very glad that Cas is taking care of things – slicking Dean’s cock with more lube, straddling his thighs, lining his hole up with his length…_

_When the angel begins the slow slide down, Dean’s whole universe narrows to the scorching heat and exquisite tightness surrounding him. As Cas is fully seated, the teen hears a sound like a wounded animal and suddenly realizes that it’s coming from himself. The older male is gasping in breath as he adjusts to the feeling of fullness, but he ignores both as he instead focuses on soothing the blond under him. Gentle fingers caress Dean’s face and slip through his hair while he breathes deeply to rein in all he’s feeling._

_A few moments later he manages to huff out, “I’m okay.” His voice is so low and rough that he momentarily sounds like his older self, and Castiel can’t help but surge forward to plunder Dean’s mouth while Cas’ body shudders atop him. He finally pulls back and rests the hand not still tangled in the teen’s hair on his chest. Then he watches sheer pleasure spread across the young face as he lifts up and shifts back down, setting an easy pace._

_Dean is enormously grateful for his earlier orgasm, as the sight and feel of the gorgeous man riding his cock is still almost too much to bear. He realizes that his hands have had a death grip on the sheets for the last few minutes, and he frees them but is at a loss for what to do with them for a moment. He’s only a little uncertain when he asks, “Cas? Can I touch you?”_

_“Always,” the angel moans fervently, and he wastes no time sliding his palms up to explore Cas’ chest, thumbs circling hardened nipples. He lingers there momentarily, enjoying the pleased hum he gets in response, before he traces his fingertips over the curves and valleys of the brunet’s toned abs. Eventually, Dean glides his hands down muscular legs then back up to grasp sharp hipbones. Dean’s grip molds to Castiel’s form like they are made for one another, and as far as the angel is concerned, they are. The teen’s hands simply guide at first, but when Cas shifts his hips just right and Dean’s cock strikes his prostate, the half-broken “Ah!” that punches out of the brunet’s mouth is just beautiful._

_The young hunter pulls Cas’ hips down harshly, angling that same way and is rewarded with the same sound, a stream of “Ah, ah, ah!” with each thrust. Their rhythm turns frantic, Castiel slamming down hard over and over while Dean yanks him onto his thrusts up from the bed. “Oh, Dean…” the angel moans. The teen feels fire coiling in his gut as that dark voice seems to scrape over his body, “Oh God, Dean! Fuck! So good. So… good…”_

_Dean is stunned when Castiel comes without warning, clenching brutally around the hardness inside him, pulsing hot ropes of white onto their bellies, cock completely untouched. The angel continues to move over him, riding out his orgasm, and the spasms of his ass finally drive Dean over the edge, releasing his seed deep within the other man._

_Cas collapses onto the teen’s chest, and Dean’s arms come around him without a second thought. He cards his fingers through sweat-dampened hair as they both gasp for breath and wait for their hearts to slow. Dean feels himself slip out of Castiel as he softens, and it’s only then that he notices the older man is already hard again. He squirms a little as his own dick gives a valiant twitch, and he comes to a decision. His voice is barely above a whisper due to anxiety, but the angel’s head snaps up so their eyes can meet when Dean murmurs, “I want you inside me…”_

_“You don’t have to do that, Dean,” the brunet insists, but the concern and tenderness in his eyes just makes Dean more certain that it’s what he wants._

_The young man cups Castiel’s face with both hands as he brings their mouths together for a thorough and gentle kiss. They rest their foreheads against one another, and Dean’s voice is louder and surer when he repeats, “I want you inside me, Cas.”_

_The look of awe and borderline-adoration on Cas’ face as he lifts up is making Dean uncomfortable, so he arranges himself on hands and knees without being asked to get away from it. He feels Castiel shift around behind him, and he expects to feel fingers at his entrance. What he doesn’t expect are Cas’ hands spreading his cheeks apart and the completely foreign sensation of a tongue sweeping across his hole._

_The air is punched from his lungs as that tongue flicks and swirls, and it takes several long moments for Dean to gasp in another breath. The angel licks from his entrance down to his balls and back up, and the teen just writhes, fingers white-knuckled in the sheets, cock beginning to fill once more. Castiel stiffens his tongue to work it past the rim so he can fuck in and out of Dean’s hole, and the slight rasp of stubble against that sensitive skin just makes it that much better._

_Cas seems to be enjoying himself if the moans he releases are anything to go by, and the vibrations travel right up inside Dean. When the tongue withdraws, it is only to be replaced with one slick finger that slides in effortlessly. The angel continues licking Dean’s rim as he thrusts his finger for long moments before adding a second. He scissors them, and any discomfort from the stretch disappears as soon as he licks his way between them to rub against Dean’s inner walls. He’s fully hard again, dripping precum onto the bed._

_The hunter’s arms give out, leaving him with his chest and shoulders pressed into the mattress, ass in the air, and he moans in tortured delight. His breath catches when he feels the third finger go in, and it ceases entirely when Castiel finds his prostate. It’s only Cas’, “Breathe, Dean,” whispered against his tailbone that allows him to drag in a ragged lungful of air. Dean keens with each swipe over that little bundle of nerves, and his body seems to just surrender to whatever is Castiel’s will._

_Cas eases his fingers out and slicks his erection with the extra lube. As he lines himself up, he twines the fingers of his other hand in the back of blond hair to turn Dean’s head just enough to catch his hazed emerald eyes. “Are you sure?” he asks one last time. The teen only nods enthusiastically._

_Castiel works his way into Dean in one slow, smooth motion that leaves him struggling for control. He’s been inside Dean before, of course – but older, experienced Dean. This Dean is untouched, and that thought kind of blows his mind._

_Dean is trembling beneath the angel, just trying to process the new feeling. There is no pain – Cas prepared him well – but the fullness and intensity are overwhelming. When the brunet slips both hands under the boy’s shoulders and lifts him until his back is flush against Castiel’s chest, the angle of his cock changes, and Dean releases the most broken noise the angel has ever heard from the blond._

_He leaves one arm holding the teen to his body and works one hand down to circle his erection, but as soon as he grazes the skin, Dean goes rigid. “Don’t, Cas. Too…” He can’t finish the thought and breaks off in a whimper._

_Fearing he has hurt his hunter, Castiel starts to pull away, apologizing as he does, “I’m sorry, Dean. I was too rough. It’s too-“_

_“Too. Good,” Dean grates out, slinging one arm behind him to grip the other man’s body so he can’t move away. He feels Cas sigh in relief, and the angel just strokes Dean’s chest and flank soothingly for a while. Finally, the tension coiled in the teen’s spine releases a bit, and he’s able to beg, “Castiel, please.”_

_He can feel the rumble of assent from Cas’ chest roll through his entire body as the angel’s grip settles on one hip, and he slowly pulls out. The noise Dean makes when Castiel thrusts back in sounds like he’s dying – but in a good way. As Cas sets a rhythm, the blond’s head falls back to rest on his shoulder, and he can only pant like he’s just run a marathon._

_Castiel holds Dean in his lap like the precious thing he is as he works inside him, all the while kissing and licking and sucking at his neck and jaw and shoulder. He ghosts his lips along the teen’s ear and murmurs, “Beautiful,” but Dean manages a derisive sound and shakes his head. Cas will not stand for this._

_The angel breaks pace and holds perfectly still to get the young man’s attention. When he can tell he has Dean’s focus, he gives one measured thrust for each statement. “Yes, Dean, you are beautiful. You are kind. You are brave. You are selfless.” Cas’ speed increases slightly as he continues vehemently, “The light of you burns through the darkness. The good in you casts away evil.”_

_Dean’s eyes are clenched shut as he rides Castiel’s intensifying movement. One hand grips the forearm banded across his chest to hold him up, and the other fumbles back to anchor into raven hair. All he can do is hold on and try not to drown in the pleasure of Castiel’s body, voice, and reverence. Their bodies are almost slamming together now, and the angel’s voice would sound terrifying were it not for the words of praise and the clear tone of adulation. “You are strong. And gentle.”_

_Castiel is beginning to lose his thread of control, but he presses on, determined to fill Dean’s soul along with his body. “You are loving. And loved.” Cas gasps and clutches the blond tighter, “Oh,_ **God** _, you are loved, Dean Winchester…” They’re both shaking so hard it’s surprising they can still cling to one another, but the angel persists. “Your soul is the beacon that guides me. You are my everything, Dean.”_

_His voice is little more than a ragged breath when he whispers, “I love you,” and Dean comes with a wail. His fingers grip Cas so hard it makes even the angel wince, but the vice of Dean’s ass gripping his cock sends him headlong into orgasm despite the pain._

_Castiel closes his eyes…_

...And opened them to meet the confused and shocked stare of _his_ Dean. “Cas? What the hell?” the hunter asked gruffly, voiced still laced with sleep. He seemed to contemplate for a moment before coming to a realization. “I remember my first time. But I also remember it with you.”

Castiel grinned a bit sheepishly. “I told you I couldn’t change the reality of your past, but there was no reason I couldn’t add another reality to your memory.” The angel paused, looking worried. “Are you angry? Should I not have…?”

Dean huffed a laugh and drew Cas’ lips briefly to his own. “I’m not mad,” he assured. “You just have some crazy ideas sometimes.”

The angel could only shrug at that, and offered the only explanation that mattered, “I love you, Dean Winchester.”

The hunter rolled his eyes as he settled back down against his lover’s chest (three rounds of angel-mojo-dream-sex apparently still really took it out of a guy). “I love you, too,” he paused a beat, “Freaking angel.”

He couldn’t see Castiel’s goofy smile, but Dean knew it was there all the same.

**Author's Note:**

> Rape/Non-Con is in the past by OMC's with underage Dean. Dean discusses his past as an underage prostitute when he was 15 in graphic detail. Cas and Dean have angel-mojo-assisted dream sex with Dean as he was when he was 15.


End file.
